Sodium hydride → 6-(3,3-Dimethyl-1,5-dioxa-spiro[5.5]undec-9-yloxy)-nicotinonitrile

HRID 459913

Reaktionsgleichung

Reaktionsgleichung von HRID 459913
[CH3:1][C:2]1([CH3:14])[CH2:7][O:6][C:5]2([CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)[O:4][CH2:3]1.[H-].[Na+].Cl[C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][N:19]=1>CN(C=O)C>[CH3:1][C:2]1([CH3:14])[CH2:3][O:4][C:5]2([CH2:8][CH2:9][CH:10]([O:13][C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][N:19]=3)[CH2:11][CH2:12]2)[O:6][CH2:7]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 124700963,3-Dimethyl-1,5-dioxaspiro[5.5]undecan-9-ol

Produkt 1

HCID 184453076-(3,3-Dimethyl-1,5-dioxa-spiro[5.5]undec-9-yloxy)-nicotinonitrileAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

Add dropwise a solution of 3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-ol, (1445 mg, 7.22 mmol) in DMF (2.1 mL) to a suspension of sodium hydride (433 mg, 10.82 mmol) in DMF (8.6 mL). Let the reaction mixture stir at room temperature for 1 h, then heat while stirring at 50° C. for 20 min. Add dropwise a solution of 6-chloro-nicotinonitrile (1200 mg, 8.66 mmol) in DMF (4.5 mL). Continue the heating at 60° C. and stirring overnight. Concentrate the reaction mixture to remove DMF. Wash the residue with water (15 mL) and extract with EtOAc/hexanes (20 mL). Dry the organic layer over sodium sulfate, filter and concentrate. Purify the residue by flash chromatography (eluent CH2Cl2/hexanes 2/1) to give 2000 mg (92% yield) of the title compound.

Aufarbeitung

  1. temperatureheat
  2. stirringwhile stirring at 50° C. for 20 min
  3. customheating at 60° C.
  4. stirringstirring overnight
  5. concentrationConcentrate the reaction mixture
  6. customto remove DMF
  7. washWash the residue with water (15 mL)
  8. extractionextract with EtOAc/hexanes (20 mL)
  9. dry with materialDry the organic layer over sodium sulfate
  10. filtrationfilter
  11. concentrationconcentrate
  12. customPurify the residue by flash chromatography (eluent CH2Cl2/hexanes 2/1)

Quellen und Nachweise

ORD-Eintrag
ord-7fd049bb6c804c0db6912e735e1eff81
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196100B2

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